Dichloromethane → 1-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 971133ノート

反応式

HRID 971133 の反応式
[F:1][C:2]([F:16])([F:15])[C:3](Br)=[N:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.CC[N:19]([CH2:22][CH3:23])CC.[CH2:24](Cl)Cl.CCO[C:30]([CH3:32])=[O:31]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[C:32]3[C:30](=[O:31])[NH:19][CH2:22][CH2:23][C:24]=3[C:3]([C:2]([F:16])([F:15])[F:1])=[N:4]2)=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8857Ethyl Acetate2 回HCID 713581942,2,2-Trifluoro-N-(4-methoxyphenyl)ethanehydrazonoyl bromide

生成物 1

HCID 218914731-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one収率 39%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

Part B. The product from Part A (5.50 g, 41.98 mmol) and 2,2,2-trifluoro-N-(4-methoxyphenyl)-ethanehydrazonoyl bromide (12.90 g, 43.58 mmol) were stirred in toluene (100 mL) at room temperature under N2. Et3N (28.0 mL, 200.1 mmol) was then added. The mixture was stirred at 85° C. for 15 h. It was cooled to room temperature and extracted with EtOAc (3×). The organic layers were washed with H2O (2×) and brine (2×), dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=4:1, then EtOAc) to produce 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one as a light-tan solid (5.09 g, yield: 39%). LC/MS (ESI+) 312.4 (M+H)+.

後処理

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layers were washed with H2O (2×) and brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

出典と根拠

ORDレコード
ord-6570251ad94b48ee9ff90b10fa503698
出典データセット
uspto-grants-2007_12
特許番号
US07312214B2

反応ノート

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